(2R)-4-carbamoyl-2-[(2R)-3-(4-hydroxyphenyl)-2-{[(1S,4R,7S,12S,15S,18S,21S,24S,30S,33S,36S,42S,45R,50S,53S,56S,59S,62S,65S,68R,75S,78S,84S,89R,92R,95S)-15,42,62,75,78-pentakis(4-aminobutyl)-24-benzyl-4,36-bis(3-carbamimidamidopropyl)-50-[(2S)-3-carboxy-2-[(2R)-2-[(2R)-3-carboxy-2-[(2R,3S)-3-hydroxy-2-[(2R)-2-{[(2S)-5-oxopyrrolidin-2-yl]formamido}-3-phenylpropanamido]butanamido]propanamido]-3-methylbutanamido]propanamido]-65-(2-carboxyethyl)-18,33-bis(carboxymethyl)-53,59,92-tris(hydroxymethyl)-89-(1H-indol-3-ylmethyl)-21-(2-methylpropyl)-84-[2-(methylsulfanyl)ethyl]-2,5,13,16,19,22,25,28,31,34,37,40,43,51,54,57,60,63,66,74,77,80,83,86,87,90,93,96-octacosaoxo-30,56,95-tris(propan-2-yl)-9,10,47,48,70,71-hexathia-3,6,14,17,20,23,26,29,32,35,38,41,44,52,55,58,61,64,67,73,76,79,82,85,88,91,94,97-octacosaazatricyclo[43.27.14.11^{12,68}]heptanonacontan-7-yl]formamido}propanamido]butanoic acid

• ChemBase ID: 105155
• Molecular Formular: C179H274N50O55S7
• Molecular Mass: 4230.84786
• Monoisotopic Mass: 4227.82256012
• SMILES: N1[C@@H](CCC1=O)C(=O)N[C@@H](C(=O)N[C@H]([C@@H](O)C)C(=O)N[C@@H](C(=O)N[C@H](C(C)C)C(=O)N[C@H](C(=O)N[C@H]1C(=O)N[C@H](CO)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](CO)C(=O)N[C@@H](CCCCN)C(=O)N[C@H](CCC(=O)O)C(=O)N[C@H]2C(=O)N[C@H](C(=O)N[C@H](CO)C(=O)N[C@H](C(C)C)C(=O)N[C@@H]3C(=O)N[C@H](CCCCN)C(=O)N[C@H](C(=O)N[C@H](CC(C)C)C(=O)N[C@H](C(=O)NCC(=O)N[C@H](C(C)C)C(=O)N[C@H](C(=O)N[C@@H](CCCNC(=N)N)C(=O)NCC(=O)N[C@H](CCCCN)C(=O)N[C@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@H](CCCCN)C(=O)N[C@@H](C(=O)N[C@H](CCCNC(=N)N)C(=O)N[C@@H](C(=O)N[C@@H](C(=O)N[C@H](CCC(=O)N)C(=O)O)Cc4ccc(O)cc4)CSSC3)CSSC2)CCSC)CSSC1)CC(=O)O)Cc1ccccc1)CC(=O)O)Cc1c[nH]c2c1cccc2)CC(=O)O)CC(=O)O)Cc1ccccc1
• Canonical SMILES: NCCCC[C@H]1NC(=O)CNC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](NC(=O)CNC(=O)[C@H](Cc2ccccc2)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CC(=O)O)NC(=O)[C@@H](CCCCN)NC(=O)[C@@H]2CSSC[C@@H](NC(=O)[C@H](NC(=O)[C@@H]3NC(=O)[C@H](NC(=O)[C@@H](NC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](NC1=O)CSSC[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](C(C)C)NC(=O)[C@H](NC(=O)[C@@H]([C@@H](O)C)NC(=O)[C@H](NC(=O)[C@@H]1CCC(=O)N1)Cc1ccccc1)CC(=O)O)CC(=O)O)C(=O)N[C@H](CO)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](CO)C(=O)N[C@@H](CCCCN)C(=O)N[C@H](CCC(=O)O)C(=O)N[C@H](CSSC3)C(=O)N[C@@H](Cc1c[nH]c3c1cccc3)C(=O)N[C@H](CO)C(=O)N[C@@H](C(=O)N2)C(C)C)CCSC)CCCCN)CCCCN)CCCNC(=N)N)C(=O)N[C@@H](C(=O)N[C@@H](C(=O)O)CCC(=O)N)Cc1ccc(cc1)O)C(C)C
• InChI: InChI=1S/C179H274N50O55S7/c1-87(2)65-111-155(261)208-112(66-93-33-15-13-16-34-93)146(252)195-77-133(239)225-139(88(3)4)172(278)213-117(71-136(244)245)158(264)199-100(44-31-62-190-178(186)187)144(250)193-75-131(237)198-102(40-22-27-58-181)148(254)219-124-82-287-290-85-127(223-160(266)118(72-137(246)247)214-173(279)140(89(5)6)226-162(268)119(73-138(248)249)215-176(282)143(92(11)233)229-161(267)114(67-94-35-17-14-18-36-94)209-153(259)107-51-54-130(236)196-107)171(277)217-122(80-232)165(271)227-141(90(7)8)174(280)218-120(78-230)163(269)201-103(41-23-28-59-182)149(255)204-108(52-55-134(240)241)154(260)222-126-84-288-286-81-123(220-151(257)105(43-25-30-61-184)200-147(253)101(39-21-26-57-180)197-132(238)76-194-145(251)109(56-64-285-12)205-167(124)273)166(272)203-106(45-32-63-191-179(188)189)152(258)221-125(169(275)210-113(68-95-46-48-97(234)49-47-95)156(262)206-110(177(283)284)50-53-129(185)235)83-289-291-86-128(168(274)202-104(42-24-29-60-183)150(256)212-116(70-135(242)243)159(265)207-111)224-175(281)142(91(9)10)228-164(270)121(79-231)216-157(263)115(211-170(126)276)69-96-74-192-99-38-20-19-37-98(96)99/h13-20,33-38,46-49,74,87-92,100-128,139-143,192,230-234H,21-32,39-45,50-73,75-86,180-184H2,1-12H3,(H2,185,235)(H,193,250)(H,194,251)(H,195,252)(H,196,236)(H,197,238)(H,198,237)(H,199,264)(H,200,253)(H,201,269)(H,202,274)(H,203,272)(H,204,255)(H,205,273)(H,206,262)(H,207,265)(H,208,261)(H,209,259)(H,210,275)(H,211,276)(H,212,256)(H,213,278)(H,214,279)(H,215,282)(H,216,263)(H,217,277)(H,218,280)(H,219,254)(H,220,257)(H,221,258)(H,222,260)(H,223,266)(H,224,281)(H,225,239)(H,226,268)(H,227,271)(H,228,270)(H,229,267)(H,240,241)(H,242,243)(H,244,245)(H,246,247)(H,248,249)(H,283,284)(H4,186,187,190)(H4,188,189,191)/t92-,100-,101-,102-,103-,104-,105-,106+,107-,108-,109-,110+,111-,112-,113+,114+,115?,116-,117-,118-,119+,120-,121+,122-,123+,124-,125+,126?,127?,128?,139-,140+,141-,142-,143+/m0/s1
• InChIKey: QWGRLMXXDYLRBA-WOBJSYDHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-4-carbamoyl-2-[(2R)-3-(4-hydroxyphenyl)-2-{[(1S,4R,7S,12S,15S,18S,21S,24S,30S,33S,36S,42S,45R,50S,53S,56S,59S,62S,65S,68R,75S,78S,84S,89R,92R,95S)-15,42,62,75,78-pentakis(4-aminobutyl)-24-benzyl-4,36-bis(3-carbamimidamidopropyl)-50-[(2S)-3-carboxy-2-[(2R)-2-[(2R)-3-carboxy-2-[(2R,3S)-3-hydroxy-2-[(2R)-2-{[(2S)-5-oxopyrrolidin-2-yl]formamido}-3-phenylpropanamido]butanamido]propanamido]-3-methylbutanamido]propanamido]-65-(2-carboxyethyl)-18,33-bis(carboxymethyl)-53,59,92-tris(hydroxymethyl)-89-(1H-indol-3-ylmethyl)-21-(2-methylpropyl)-84-[2-(methylsulfanyl)ethyl]-2,5,13,16,19,22,25,28,31,34,37,40,43,51,54,57,60,63,66,74,77,80,83,86,87,90,93,96-octacosaoxo-30,56,95-tris(propan-2-yl)-9,10,47,48,70,71-hexathia-3,6,14,17,20,23,26,29,32,35,38,41,44,52,55,58,61,64,67,73,76,79,82,85,88,91,94,97-octacosaazatricyclo[43.27.14.11^{12,68}]heptanonacontan-7-yl]formamido}propanamido]butanoic acid
• IUPAC Traditional name: (2R)-4-carbamoyl-2-[(2R)-3-(4-hydroxyphenyl)-2-{[(1S,4R,7S,12S,15S,18S,21S,24S,30S,33S,36S,42S,45R,50S,53S,56S,59S,62S,65S,68R,75S,78S,84S,89R,92R,95S)-15,42,62,75,78-pentakis(4-aminobutyl)-24-benzyl-4,36-bis(3-carbamimidamidopropyl)-50-[(2S)-3-carboxy-2-[(2R)-2-[(2R)-3-carboxy-2-[(2R,3S)-3-hydroxy-2-[(2R)-2-{[(2S)-5-oxopyrrolidin-2-yl]formamido}-3-phenylpropanamido]butanamido]propanamido]-3-methylbutanamido]propanamido]-65-(2-carboxyethyl)-18,33-bis(carboxymethyl)-53,59,92-tris(hydroxymethyl)-89-(1H-indol-3-ylmethyl)-30,56,95-triisopropyl-21-(2-methylpropyl)-84-[2-(methylsulfanyl)ethyl]-2,5,13,16,19,22,25,28,31,34,37,40,43,51,54,57,60,63,66,74,77,80,83,86,87,90,93,96-octacosaoxo-9,10,47,48,70,71-hexathia-3,6,14,17,20,23,26,29,32,35,38,41,44,52,55,58,61,64,67,73,76,79,82,85,88,91,94,97-octacosaazatricyclo[43.27.14.11^{12,68}]heptanonacontan-7-yl]formamido}propanamido]butanoic acid
• Synonyms: IBTX; IBTX (SCORPION, BUTHUS TAMULUS); pGlu-Phe-Thr-Asp-Val-Asp-Cys-Ser-Val-Ser-Lys-Glu-Cys-Trp-Ser-Val-Cys-Lys-Asp-Leu-Phe-Gly-Val-Asp-Arg-Gly-Lys-Cys-Met-Gly-Lys-Lys-Cys-Arg-Cys-Tyr-Gln [Disulfide Bridges: 7?28; 13?33; 17?35]; IBERIOTOXIN

Database IDs

• CAS Number: 129203-60-7
• PubChem SID: 162091946
• PubChem CID: 71299710

CALCULATED PROPERTIES

• Acid pKa: 2.7470853
• H Acceptors: 66
• H Donor: 61
• LogD (pH = 5.5): -30.795197
• LogD (pH = 7.4): -37.315395
• Log P: -24.76212
• Molar Refractivity: 1068.783 cm^3
• Polarizability: 412.05682 Å^3
• Polar Surface Area: 1714.43 Å^2
• Rotatable Bonds: 80
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: No data
• Boiling Point: No data
• Flash Point: No data
• Auto Ignition Point: No data
• Density: No data
• Vapor Pressure: No data
• Vapor Density: No data
• Partition Coefficient: No data

Safety Information

• Storage Condition: 0°C
• RTECS: NH6107500
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 3172
• Hazard Class: 6.1
• Packing Group: III
• Australian Hazchem: 2X
• Risk Statements: R:25
• Safety Statements: S:28-36/37/39-45-53
• EU Classification: T2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 153

Product Information

• Purity: 98%

DETAILS

MP Biomedicals - 02158935

From Buthus tamulus Scorpion
Purity: 98%
More specific than charybdotoxin at inhibiting high conductance Ca2+-activated K+ channel via allosteric inhibition.

REFERENCES

• Galvez, A., et al., J. Biol. Chem., 265: 11083 (1990)
• Essin, K., et al., BK Channels In Innate Immune Functions Of Neutrophils And Macrophages. Blood 113, 1326-31, (2009)
• Galvez, A., Purification and characterization of a unique potent peptidyl probe for the high conductance calcium-activated potassium channel from venom of the scorpion Buthus tamulus. J. Biol. Chem. 265, 11083, (1990)
• Candia, S. et al., Mode of action of Iberiotoxin, a potent blocker of the large conductance Ca2+-activated K+ channel. Biophys. J. 63, 583-90, (1992)
• Satake, N., et al., The inhibitory effects of iberiotoxin and 4-aminopyridine on the relaxation induced by β1- and β2-adrenoceptor activation in rat aortic rings. Br. J. Pharmacol. 119, 505, (1996)
• Shao, L.R., et al., The role of BK-type Ca2+-dependent K+ channels in spike broadening during repetitive firing in rat hippocampal pyramidal cells. J. Physiol. 521, 135, (1999)
• Merck 14,4874